Boc-1,3-diaminopropane HCl
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Boc-1,3-diaminopropane HCl

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Category
BOC-Amino Acids
Catalog number
BAT-007933
CAS number
127346-48-9
Molecular Formula
C8H18N2O2·HCl
Molecular Weight
210.70
Boc-1,3-diaminopropane HCl
Synonyms
Boc-NH(CH2)3NH2 HCl; tert-Butyl (3-aminopropyl)carbamate hydrochloride; N-BOC-1,3-DIAMINOPROPANE HYDROCHLORIDE; N-(3-aminopropyl)carbamic acid tert-butyl ester hydrochloride; Carbamic acid, N-(3-aminopropyl)-, 1,1-dimethylethyl ester, hydrochloride (1:1); N-(3-AMINOPROPYL)CARBAMIC ACID TERT-BUTYL ESTER HCl; N-Boc-1,3-diaminopropane HCl
Appearance
White powder
Purity
≥ 99% (Titration)
Melting Point
151-161 °C
Boiling Point
307.2 °C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C8H18N2O2.ClH/c1-8(2,3)12-7(11)10-6-4-5-9;/h4-6,9H2,1-3H3,(H,10,11);1H
InChI Key
WUXOJNUZYOFBMI-UHFFFAOYSA-N
Canonical SMILES
CC(C)(C)OC(=O)NCCCN.Cl
1. Cyclic enkephalin-deltorphin hybrids containing a carbonyl bridge: structure and opioid activity
Małgorzata Ciszewska, Katarzyna Ruszczyńska, Marta Oleszczuk, Nga N Chung, Ewa Witkowska, Peter W Schiller, Jacek Wójcik, Jan Izdebski Acta Biochim Pol. 2011;58(2):225-30. Epub 2011 May 17.
Six hybrid N-ureidoethylamides of octapeptides in which an N-terminal cyclic structure related to enkephalin was elongated by a C-terminal fragment of deltorphin were synthesized on MBHA resin. The synthetic procedure involved deprotection of Boc groups with HCl/dioxane and cleavage of the peptide resin with 45 % TFA in DCM. d-Lys and d-Orn were incorporated in position 2, and Lys, Orn, Dab, or Dap in position 5. The side chains of the dibasic amino function were protected with the Fmoc group. This protection was removed by treatment with 55 % piperidine in DMF, and cyclization was achieved by treatment with bis-(4-nitrophenyl)carbonate. Using various combinations of dibasic amino acids, peptides containing a 17-, 18-, 19- or 20-membered ring structure were obtained. The peptides were tested in the guinea-pig ileum (GPI) and mouse vas deferens (MVD) assays. Diverse opioid activities were observed, depending on the size of the ring. Extension of the enkephalin sequence at the C-terminus by a deltorphin fragment resulted in a change of receptor selectivity in favor of the δ receptor. The conformational propensities of selected peptides were determined using the EDMC method in conjunction with data derived from NMR experiments carried out in water. This approach allowed proper examination of the dynamical behavior of these small peptides. The results were compared with those obtained earlier with corresponding N-(ureidoethyl)pentapeptide amides.
2. Total solid-phase synthesis of bombesin analogs with different functional groups at the C-terminus
Wael R Abd-Elgaliel, Fabio Gallazzi, Susan Z Lever J Pept Sci. 2007 Jul;13(7):487-92. doi: 10.1002/psc.878.
Five bombesin analogs with different functional groups at the C-terminus were synthesized using a solid-phase strategy. The protocols were optimized using 4-(hydroxymethyl)benzoic acid (HMBA) resin to synthesize a common precursor followed by nucleophilic cleavage of the base sensitive peptide ester linkage. The C-terminal modifications included ethylamide, butylamide, methyl ester, propyl ester and hydrazide. Cleavage from the resin was possible with the fully protected or deprotected precursor peptide; however, higher purity of the final products was achieved when cleavage protocols were conducted after side-chain deprotection. The synthesized peptides were analyzed and characterized using reverse phase HPLC and ESI-MS. The peptides were obtained in 13-32% overall recovery, calculated from the coupling efficiency of the first amino acid residue, and in 91-97% purity.
3. N-(ureidoethyl)amides of cyclic enkephalin analogs
Małgorzata Ciszewska, Maria Kwasiborska, Michał Nowakowski, Marta Oleszczuk, Jacek Wójcik, Nga N Chung, Peter W Schiller, Jan Izdebski J Pept Sci. 2009 Apr;15(4):312-8. doi: 10.1002/psc.1118.
Novel N-(ureidoethyl)amides of cyclic enkephalin analogs have been synthesized. The p-nitrophenyl carbamate of 1-Boc-1,2-diaminoethane was coupled with 4-methylbenzhydrylamine (MBHA) resin. The Boc group was removed by treatment with HCl/dioxane, and the peptide chain was assembled using Boc strategy. For deprotection of amino function, HCl/dioxane was used. D-Lys or D-Orn were incorporated in position 2, and the side chains of Lys, Orn, Dab, or Dap in position 5 were protected with Fmoc group. Side chain protection was removed by treatment with 55% piperidine in DMF, and cyclization was achieved by treatment with bis-(4-nitrophenyl)carbonate to form a urea bridge. The peptide was cleaved from the resin by treatment with 45% TFA in DCM. The peptides were tested in the guinea-pig ileum (GPI) and mouse vas deferens (MVD) assays. Divers opioid activities were observed, depending on the size of the ring. In comparison with [Leu(5)]enkephalin, all peptides were more active in the GPI assay (between 125 and 12 times), and some of them were also more potent in the MVD assay. The conformational propensities of each peptide were determined using the EDMC method in conjunction with NMR experiments. This approach allows treating the dynamical behavior of small peptides properly. The results were compared with those obtained previously for corresponding nonsubstituted amides and are in agreement with the biologically active conformation proposed by us earlier.
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